The present disclosure provides novel organic compounds that may demonstrate activity as pesticides, meaning that they may control fungi, insects, mites, and/or animal parasites. The disclosure also provides novel pesticide methods and compositions utilizing the novel compounds.
More specifically, the invention provides new compounds of the formula (I-A):
wherein:
R is H, CH3, phenyl, or a heterocycle comprising a 5 or 6 membered single ring or a fused ring system comprising at least one 5 or 6 membered heterocycle optionally substituted with H, halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO2, CN, lower alkoxycarbonyl, lower alkylcarbonyl, lower alkyl-SOq, and aldoximes and lower alkyloximes, optionally substituted on oxygen by lower alkyl.
Z is H, a C—C single bond, CH2, NH, O, S, CN, CH2O, OCH2, CH2CH2O, or OCH2CH2;
m is 4;
p is 0 or 1;
q is an integer from 0 to 2;
R1 is independently H, halo, lower alkyl, lower alkenyl, lower alkynyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, NO2, CN, lower alkylcarbonyl, lower alkoxycarbonyl, mercapto, lower alkylthio, aldoximes and lower alkyloximes, optionally substituted on oxygen by lower alkyl;
Y is a C—C single bond, C(R5n)O or C(R5n);
n is 2;
alternatively R1m, Z, and Rp may be taken together to form a fused 5 or 6 membered heterocycle optionally substituted with H, halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO2, CN, lower alkylcarbonyl, lower alkoxycarbonyl and lower alkyl-SOq;
R2 are independently H or lower alkyl;
R4 is H, halogen, lower alkyl, lower alkoxy or lower haloalkyl;
R5 are independently H or lower alkyl;
X1 is NR3, O, and S, where R3 is selected from H, lower alkyl, lower alkylcarbonyl, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkyl-SOq, phenyl-SOq or substituted phenyl-SOq;
X2 is H, halogen or lower alkyl; and
X3 is H, halogen or lower alkyl;
with the proviso that when Y is C(R5n), R2n and R1m may be taken together to form
The invention also provides new compounds of formula (I-B):
wherein:
R is H, CH3, haloalkyl, phenyl, or a heterocycle comprising a 5 or 6 membered single ring or a fused ring system comprising at least one 5 or 6 membered heterocycle optionally substituted with H, halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO2, CN, lower alkoxycarbonyl, lower alkylcarbonyl, lower alkyl-SOq, aldoximes and lower alkyloximes, optionally substituted on oxygen by lower alkyl;
Z is H, a C—C single bond, CH2, NH, O, S, CN, CH2O, OCH2, CH2CH2O, or OCH2CH2;
m is 4;
p is 0 or 1;
q is an integer from 0 to 2;
R1 is independently H, halo, lower alkyl, lower alkenyl, lower alkynyl, hydroxy, lower alkoxy, haloalkyl, haloalkoxy, NO2, CN, lower alkylcarbonyl, lower alkoxycarbonyl, mercapto, lower alkylthio, aldoximes and lower alkyloximes, optionally substituted on oxygen by lower alkyl;
Y is a C—C single bond, C(R5n)O or C(R5n);
n is 2;
alternatively R1m, Z, and Rp may be taken together to form a fused 5 or 6 membered heterocycle optionally substituted with H, halo, lower alkyl, lower alkoxy, benzyloxy, lower alkenyl, lower alkynyl, haloalkyl, haloalkoxy, NO2, CN, lower alkylcarbonyl, lower alkoxycarbonyl and lower alkyl-SOq;
R2 are independently H or lower alkyl
R4 is H, halogen, lower alkyl, lower alkoxy or lower haloalkyl;
R5 are independently H or lower alkyl
X1 is NR3, O, and S, where R3 is selected from H, lower alkyl, lower alkylcarbonyl, lower alkoxycarbonyl, hydroxy, lower alkoxy, lower alkyl-SOq, phenyl-SOq or substituted phenyl-SOq;
X2 is H, halogen or lower alkyl; and
X3 is H, halogen or lower alkyl;
with the proviso that when Y is C(R5n), R2n and R1m may be taken together to form

The invention also provides new pesticide methods and compositions utilizing the compounds of formula (I-A) and compounds of formula (I-B).
The invention includes fungicidal, insecticidal, acaricidal, and anti-parasitic compositions comprising an effective amount of a compound of the present invention in a mixture with an agriculturally acceptable or pharmaceutically acceptable adjuvant or carrier. The invention also includes methods of controlling a fungus, insect, mite, or parasite comprising applying an effective amount of a compound of the present invention to the fungus, insect or mite, soil, plant, root, foliage, seed, locus, or animal (for which purpose they may be administered orally, parenterally, percutaneously or topically) in which the infestation is to be prevented or cured.